Taking home the Academy Award -- it wasn't officially nicknamed Oscar until 1939 -- for Outstanding Picture (later known as Best Picture) was Wings, a silent World War One Gary CoG and Charles "Buddy" Rogers, with Gary Cooper in one of his earliest roles.
Unlike the Academy Awards of today, the 1929 awards -- honouring films from '27 and '28 -- was a private affair that cost $5 to attend, and that included dinner. The ceremony itself, hosted by swashbuckler Douglas Fairbanks, lasted a mere 15 minutes and is the only one not presented on radio or tee vee. Compare this to current glitzy Oscar telecasts that have to work hard to contain themselves to 3 hours, with dozens of awards given out at a lunch ceremony earlier.
Here is the 1929 Academy Award for Outstanding Picture:
There was also no drama about the 1st Academy Awards; winners had been announced 3 months earlier. Twelve Oscars statuettes were given out that night. Stolen directly from the WikiWackyWoo:
Nominees and winners of the 1st Academy Awards
|Outstanding Picture||Unique and Artistic Production|
|Best Director, Comedy Picture||Best Director, Dramatic Picture|
|Best Actor in a Leading Role||Best Actress in a Leading Role|
|Best Writing, Original Story||Best Writing, Adapted Story|
|Best Cinematography||Best Art Direction|
|Best Engineering Effects||Best Writing, Title Writing|
Further reading at Not Now Silly